Acid wool dyestuffs



Patented Nov. 2, 1943 UNITEDYSTATES a v 2,333,137 PATENT OFFICE ACID WOOL DYESTUFFS I Werner Zerweck and Ernst Heinrich, Frankforton the-Main-Fechenheim, Germany, .assignors ,to General Aniline & Film Corporation, New

' York, N. Y., a corporation of Delaware No Drawing. Application June 14, 1940, Serial No. 340,547. In Germany July 8, 1939 2 Claims.

Our present invention relates to acid wool dyestufls more particularly to those of the general wherein It stands for a radicleof the benzene series, X for a member of the group consisting of alkylene, O-alkylene, S-alkylene, .SO-alkylene and SOz-alkylene radicles, Brand R2 for amember of the group consisting of alkyl'andhydroxw alkyl radicles and radicals which, together with the terminal nitrogen, form a-hjeterocyclic radicle, n for a number from 1 to, 3.

The process of manufacture of the pr'sent new dyestuffs according to'one feature of the invention consists in condensing a' l-amino-4-halogenanth'raquinone-Z- fonic acid with an amine of the general formulai" V 'l IN wherein X; B1 and Rrihave the jaforesaidsignification and, ifnecessary," after treating the con-- densation product formed with a sulfon'ating agent.

According to a further feature of the invention dyestuffs of the same class are obtained by condensing a. 1-amino-2.4-diha1ogen-anthraquinone with an amine of the aforesaid kind and replacing in the molecule of the condensation product the halogen atom standing in the 2-position of the anthraquinone nucleus-by the sulfonic acid group. V

The present new dyestuffs are distinguished by a particular levellingpower and dye wool from an acid bath mostly bluish shades of good fastness properties particularly of a good fastness to light.

In order to further illustrate our invention the followingexamples are given, the parts being by grade.

weightj andl all temperaturesin degrees centisulfonic acid are dissolved in about 3000 parts of water and 1000 parts of alcohol and 12 parts of 4-aminobenzyl-dimethylamine, 40 parts of sodium bicarbonate and 4 parts of'cuprous chloride are added. The mixture is heated to'bolling for some hoursand the reaction product formed is separated --by acidification and isolated. It dissolves in concentrated sulfuric acid with a bluish green color turning to yellowish green after the addition of paraformaldehyde.

(b) v Sulfonation '30 parts of the aforesaid condensation product are dissolved in a mixture of parts of sulfuric acid monohydrate and 30 parts of fuming sulfuric acid of 20% strength. The reaction mass is heated at 40 to 45 for about 20 hours and then ice is added. The dyestufl solution having a strong mineral acid reaction is then neutralized with a caustic soda lye of 33 B., ad-

vantageously while cooling. The separated dyestuff is isolated. Itcorresponds with the formula:

It dissolves in concentrated sulfuric acid with a reddish blue. color turning to yellowish green after theaddition of. paraformaldehyde.

The dyestuff dyes wool reddish blue shades of a'good fastness to light and an excellent levelling power. 1 v

When replacing the 4-aminobenzyl-dimethylamine by the equivalent amount of 4-aminobenzyl-diethyl-amine, 4-aminobenzyl-hydroxyethylamine, 4-aminobenzyl-dipropylamine of the formula:

' 4-aminobenzyl-diiso-butylamine, i-aminophen- J V I v i 40 parts of i-amino-4-bromoanthraquinone-2-' ethyl-diethylamine of the formula CaHl When replacing the 1-amino-4-bromoanthraquinone-2-sulfonic acid by equivalent amount of 1-amino-4-bromo-5-acetylaminoor -5-methoxyacetylamino-anthraquinone-2-sulfonic acid there are obtained dyestufis dyeing wool somewhat more greenish valuable shades.

EXAMPLE 5 25 parts of 1-amino-4-iodinoanthraquinone- 2.6-disu1fonic acid are dissolved in about 1500 parts of water and a solution of 15 parts of p-amino-benzyl-dimethyl-amine, 25 parts of sodium carbonate and 2.5 parts of cuprous chloride are added. The mixture is heated some hours to boiling, the formed solution is filtered off and the condensation product is isolated by adding sodium chloride thereto. It may be purifled by redissolving it. It dyes wool reddish blue shades fast to light and has an excellent levelling power.

By a subsequent sulfonation a dyestufi is obtained of the formula:

which has a very good levelling power and dyes wool reddish blue shades fast to light.

Dyestuffs of a similar valuable shade are obtained by replacing p-aminobenzyl-dimethylamine by for instance p-amino-benzyldiethyla mi n e, p amino phenetidyl diethylamine, p-amino-benzylmorpholine, p-aminobenzyl-pyrrolidine, p-amino-benzyl-piperidine or p-aminobenzyl-methyl-taurine or the corresponding or m-compounds.

We claim: 1. Acid wool dyestufis of the general formula: 5 P l w -soiH a o X sole). I

L. R: J

wherein R stands for a radicle of the benzene series, X for alkylene, R1 and R: for alkyl and n for a number from 1 to 3, said dyestuifs having a good levelling power and dyeing wool from an acid bath bluish shades of a good fastness, particularly to light.

2. An acid wool dyestufi of the formula:

SOIH 0 NH A -l-S0:H

(i'lHa N-CH: 40

CHaSOaH which dyestufi has a good levelling power and dyes wool clear reddish blue shades fast to light. WERNER ZERWECK.

. ERNST HEINRICH. 

